Interviews with Brandon Westgate all inevitably turn to the topic of cranberries. Yes, his family owns a cranberry farm but nobody needs to hear that much about cranberries. Tom the Turkey doesn’t even care that much about cranberries, so why should anyone else?

In an effort to focus on something else, we decided to pester Brandon with some goof questions and some questions I found on a speed dating website. Stuff like: outhouses vs. bathrooms, circumcision vs. not circumcision, and manual labor vs. YouTube labor.

You just turned 30, how are you feeling? What has been your favorite age so far?
Yeah, I feel great! I think I feel better now than when I was like, 20. I think my favorite age is right now, I got another kid on the way and a house.

You ever walk outside and take a piss in your backyard just because you can?
Yeah, I do that every morning.

What about jerking off in the backyard?
[laughs] Nah…

Nobody’s around, you can do whatever you want, right?
Yeah, I guess. You could jerk off all you want but it’s like, I never really had the urge to go outside and jerk off. It’s like looking at the trees and shit, you know?

It’s closer to nature, better oxygen.
Yeah, I guess…

What was Zoo York paying you at your peak when you rode for them?
Oh yeah, definitely not going to share that [laughs]. It was good but it was definitely not as good as Chaz [Ortiz]. I think Chaz was making double what I was making, and I was making pretty good money.

How long does a Zoo York contract last? What’s industry average?
Mine were like 3 or 4 years at a time. My Emerica one was always for 3 years. If they give you a shoe, it takes a while to make it and promote it so if you only had a 1 year contract, it’s kinda a waste of time for them.

Rob Dyrdek said once that when you’re in the prime of your career, try to negotiate shorter contracts with your sponsors and negotiate every year for more pay and when you’re older try to milk it and do 3+ year contracts.
Yeah, I don’t know. I never had an agent or anything like that, a lot of dude have that and the agent like advises you and do all the talking. But I’ve kind of just ran it myself, I just take more or less what they offer; you could only argue so much.

You’ve had a pretty successful pro career for the last 10 years, but do you think you could have been even bigger if you dressed crazier and had a more outlandish image?
I don’t think that would work for me because I wouldn’t know how to dress. I used to get made fun of when I was wearing those Zoo York shirts all the time, you know? I just never gave a shit because I’m riding for this brand and they’re paying me so whatever, I’m going to back it.

Buying more clothes feels like a waste of money when I get them for free and I’m supposed to wear these clothes already anyway. So I would probably end up just looking like an idiot. You know those people who start trends? I’m somebody who would be following it. I don’t think that would really work for me.

You would have to smoke spliffs and give the middle finger to the camera a lot.
I would rather do the opposite. ‘Cause once that trend starts, everybody is doing it. No one stands out at a certain point. I would rather do my own thing. I have just been doing the same thing for so long. It works, so I don’t know why I would change it.

Would you consider yourself basic?
I’m pretty basic, yeah. I just wear skate clothes and I just skate what I like to skate. Which isn’t any super thought-out thing.

Do you ever feel like skating as a profession can hold you back because when it’s over or if you get hurt, you’re left with not much?
Yeah, the fear of getting hurt and seeing older guys struggle. You get caught up making good money and spending it fast. [Aaron] Suski and Donny [Barley] were killing it and then when they were done they were lost. Donny found his way and he works at Element now, and he’s killing it now. But it was crazy to watch him go through that struggle. He was fucking Donny Barley and then he was doing landscaping and looking for work. I don’t have any education or anything either, I got married and planned to have kids and stuff, so you have to think of something to like feed them.

Yeah, I think Bobby Puleo works around the corner from me at a restaurant.
Yeah, exactly. And it’s not like farming is going to pay out the ass, but my dad has done it forever and supported us, so it’s hard work and you put in the hours but it’s something I like to do. It’s like skating, if you find something you love, you’re not working that hard.

Growing up I heard you built a dope underground fort in the woods. What was it like?
This fort was literally just a hole in the ground that was hollowed out and it had two trees growing across of it, and then someone put plywood over it. It was underground and you wouldn’t be able to see it. You just put leaves and shit over it so no one would ever know. It was maybe 10 feet long and 10 feet wide. We were able to stand up in there with 4 or 5 people.

It collapsed over the years and when it would rain it would all fill up with water so you couldn’t even go down there. But we put a stove down in there and found an old couch. My friend slept on the couch and I was like, “Damn dude, how did you sleep down there? That’s fucking gnarly.” I would never do that. Once we built it we were kind of done with it.

18 and 19-year-olds today probably don’t have that mentality to physically build something or do real, old school work. A lot of people in our generation are kind of wimpy.
Definitely a change in times, that’s for sure. Even the whole cranberry thing, it’s hard to find younger guys who want to do that work because nowadays you can just film yourself and get paid off YouTube. Nobody wants to work like that anymore.

“It’s hard to find younger guys who want to do that work because nowadays you can just film yourself and get paid off YouTube.”

Do you think social media is wack?
I just do Instagram. Facebook – that shit is a joke to me. I don’t even understand it. People posting their mood and shit. With social media it’s almost if everyone is bragging, “Look at me, look at me.” Back in the day that was wack to be like, “Look at all this shit I’ve been doing everyday!”

One time [Anthony] Shetler told me he posted this thing like, “Why is it rude to ask women their weight?”, and he’s reading all these responses. I was like, “Why would you even bother posting that?” And he was like, “I just wanted to see people’s reactions.” I feel like Facebook is just a lot of that.

Just weird reactionary stuff?
Yeah, just people trying to get people worked up. It’s weird to me because I feel like it’s so fake. People feel like they have this voice on social media, but is anyone going to say anything to your face? Is anyone going to go ask a woman their actual weight? No, but it’s fine to post that out there and stir up people’s emotions and reactions. It just seems pointless to me.

You must be pretty jacked from working on a farm, right?
Well, the farm helps with the top half. I dry pick the cranberries so I have to carry all the bags. By the end of it your arms feel pretty stringy. You get kind of beat up but you’re physically in shape. Even now, it’s winter time and I heat the house with a wood stove. We have a furnace but I try to keep the cost down by splitting the wood. You cut the wood, split the wood, and then carry it into the house, fill the stove, so you’re always doing something.

Dude, you’re living in the 1800s over there!
[Laughs] A lot of people live like that out here. There are trees around so we use them to heat it up.

You got an outhouse out there or are you flushing toilets?
Oh no, I’m flushing toilets. Actually, our house is pretty dope. It’s a nice house [laughs].

Are you trying to get your kids skating?
I cruise around and put my daughter on the front of the board. She loves it. Having a 2-and-a-half-year-old, you can’t really teach them how to skate. They just mob around and do whatever they want. Kids want to do the opposite of what you tell them so you can’t really beat anything into their brains because they’re going to want to defy you.

You talked about some circumcision documentary on Anthony Shetler’s podcast. What’s that about?
My wife wanted to watch it before we knew if we were going to have a girl or a boy because it was like, are we going to do that? I was all for it because I’m circumcised so fuck it, isn’t that the tradition? But I watched it and it was saying that the U.S. is the only country that does it, but there’s no reason for it basically. They’ve come up with all these things about it helping with STDs or all this bullshit, and it’s all made up shit.

You’re a day old and they take you and chop the skin of your dick off when it’s not necessary. And the kid doesn’t have the decision, so they’re arguing that the kid should have the right as a human. So after watching it, I was like I wouldn’t do this to my kid. A lot of the time they don’t use any pain medication and the apparatus that they use is pretty gnarly and they could fuck your dick up. I would feel horrible if I did this thing to my child that was unnecessary and his dick was ruined. That’s a huge part of your life.

Yeah, it’s pretty important to most of us.
They tried to argue that it’s for sanitary reasons, but you’re born with that skin. It’s not meant to be chopped off. They’re probably just making extra dollars off of it or something.

They were saying that people that have the skin, their dick is more sensitive, so actually, your sex life should be better because it’s not rubbing against shit all the time. Also, the doc was saying that the kids just go into shock because of the pain. Imagine them taking your skin right now. It would be traumatizing and painful.

But you said there was a method of getting the foreskin back? Like growing it back or having it reattached?
Yeah, there’s this attachment that stretches the skin. There was a guy on there that uses that. They didn’t show it or anything, but supposedly he grew his foreskin back.

You trying that foreskin regenerator on yourself?
[Laughs] No.

If money didn’t matter to you, what would your life be like?
I would definitely stay here. I would build a skatepark and update it every year based on everyone’s ideas. I would start my own farm other than just cranberries. I would grow everything I wanted to because that’s something I enjoy doing. I like being outside and people need to eat. People don’t know what they are eating, that’s the main problem. Half this shit wouldn’t fly if people knew and cared about what they were eating.

You’re saying that people need better food education?
Yeah, just in general. Did you hear about that dude Andrew Lang? He’s running for president. He had a Joe Rogan podcast and he goes in about truck drivers. Like, there are 3 million truck drivers, but they are going to automate that job in the future. Everything is going that way, so it’s just a matter of time before all these people don’t have jobs and it’s a huge crisis.

Won’t farming become automated too?
Farming is already automated to a point. A lot of peoples’ irrigation pumps are automated. Mine is. But more complicated tasks… A robot is not going to go to your house, cut up pipe, find a measurement for a pipe, that’s a really hard job to automate. Eventually it probably will be, but I don’t think in my time.

Eventually, if 50% of the population doesn’t have jobs, no one is going to be able to afford their bills or anything. You can’t take someone who has been driving a truck for the past 25 years and expect them to know some computer programming.

If you could meet anyone from the past, who would it be?
Maybe my grandpa. He died when I was two so I never got to hang out with him. He probably had some cool stories and I would just chill with him for a day.

You would really rather meet your grandpa than like, Houdini or someone more famous?
Yeah, dude. I don’t know what I’m going to talk to Houdini about for the whole day. I got no questions for him [laughs]. My grandpa’s part of my family so I’d feel more comfortable with him. I don’t want to hang out with some random stranger that I don’t really know. What am I going to ask him? “How did you figure out how to magically do that?” I don’t really care. He’s probably a cool guy, but I feel like it would get awkward. My grandpa would probably be hyped to chill with me as well, so it’s a mutual thing.

How much money would I have to pay you to take a hit of crack?
Oh shit, how much would you offer?

$500.
It’s got to be more than that. I’m thinking like something that I can buy something with, like a new truck.

$5,000.
I don’t know. If you had the cash in front of me and you hit the crack first and were like, “Shit’s chill,” I’d be like, “Alright.” Someone I knew growing up got into crack. I was like, “What the fuck is crack anyway?” So we looked it up, it said that the high only lasts 15 minutes. And you have a small pipe because when it gets into the air it loses its potency.

“I’ve never smoked crack, but I’m curious about all of that and how cool it really is.”

What’s scary is I think the crack high is so good, you’re going to be thinking about it in the future.
Dude, I always wonder about that shit! There’s so many heroin addicts in this area. I’ve never even taken a Percocet because I was terrified of that shit. I mean, is it really like, if you take one hit of crack you really are just done after that? And is crack that easy to find? I wouldn’t even know where to find crack around here.

I think also a lot of those people are in mentally vulnerable places. They are like, “This is way good because my life fucking sucks.” But then again I have no idea, I’ve never smoked crack. But I’m really curious about all of that and how cool it really is.

Me too. Heroin has got to be insanely good.
Yeah, no. Everyone loves the shit. I think when I’m super old and about to die maybe I’ll try all that shit.

It’s the best high you can get in your entire life. It’s the only drug the government can’t ban.
Wait, so you’ve done that? That would be my last resort if I was fully cracked out. Like if I was having withdrawals I’ll go to that. You never know when I’ll need that.